Non-iTunes downloaded songs are becoming corrupted, starting with album art

I have Windows Vista, and I just got a new refurbished iPod touch 64gb 5th gen.
For some reason, songs that I have downloaded (not from iTunes) are becoming corrupted?? some are even old songs I have downloaded months ago but most of this seems to be with songs stuff I haven downloaded recently. This literally just happened yesterday. The album art is showing up on iTunes as half downloaded or with a broken, glitchy bar after I sync to my iPod. Then, most of those songs are corrupted, making those skipping noises in the song. What is even stranger is that most of these messed up songs are ONLY messed up on iTunes, on my iPod they're fine, but then some of them get corrupted on both. I use a "Passport" EXTERNAL hard drive, could there be a problem with that?? Everything I have downloaded is saved to that external hard drive and like I said, even some of the old songs I downloaded months, even years ago are having the album art problem and some of them the sound quality corruption.
I tried restarting and re downloading iTunes hitting the "repair" option, but I think this may be the external hard drives problem?
Does anyone know what I should do? Am I asking this question in the correct place?
Message was edited by: foresttemple

I can't seem to get album art to download into some of my songs. I compare my song information with the information that's in the iTunes music store & it matches word for word but it won't download the art. I can understand if iTunes didn't have the album but they do & the art wont download at all. I click "get album art" so many times & nothing shows up.

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No, I do not want to "factory reset" my iPod. No I do not wish to do anything crazy long or hard to fix this.
That may be necessary, It is not what you want to do/not do but what is required to resolve your problem.

Non-iTunes downloaded songs are becoming corrupted, starting with album art

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